Transportation Supervisor

About the role

We are seeking a Transportation Supervisor to oversee our transportation services and ensure safe, reliable transportation for the individuals we support across Connecticut and New York. In this role, you'll lead a team of drivers and transportation aides, manage daily transportation operations, coordinate fleet maintenance, optimize routes, and serve as a key problem-solver for transportation-related needs.

Responsibilities

• Lead Transportation Operations
  • Oversee the day-to-day operations of the transportation department.
  • Supervise, coach, mentor, and develop Transportation Drivers and Transportation Aides.
  • Manage hiring, onboarding, training, scheduling, and performance management activities.
  • Ensure adequate staffing coverage by coordinating schedules, vacations, call-outs, and leaves.
  • Assign and dispatch drivers to routes and community locations.
  • Respond to transportation emergencies, service disruptions, weather impacts, and schedule changes.
  • Serve as the primary transportation resource for operational issues during business hours.
• Manage Scheduling & Service Delivery
  • Coordinate transportation schedules and route assignments across programs.
  • Partner with Program Managers and agency leadership to ensure transportation needs are met.
  • Continuously evaluate routes to maximize efficiency while maintaining excellent customer service.
  • Adapt schedules based on individual needs, staffing changes, vehicle availability, and program requirements.
• Support Driver Success
  • Provide ongoing coaching, feedback, and performance evaluations.
  • Ensure compliance with required agency, state, and regulatory training requirements.
  • Maintain driver qualifications and certifications.
  • Promote a culture of safety, accountability, and excellent customer service.
• Oversee Fleet Operations
  • Coordinate vehicle maintenance, inspections, repairs, registrations, and vendor appointments.
  • Monitor fleet utilization and recommend improvements to increase efficiency.
  • Ensure all agency vehicles remain compliant with transportation regulations in Connecticut and New York.
  • Work closely with maintenance vendors to minimize vehicle downtime.
• Utilize Transportation Technology
  • Manage transportation data and records using systems such as Salesforce, Evolv, Azuga, and UKG Pro.
  • Monitor GPS and driver safety technology.
  • Analyze transportation trends, vehicle usage, operational metrics, and safety data.
  • Identify opportunities to improve efficiency and reduce operating costs.
• Be a Communication Hub
  • Build strong partnerships with individuals served, families, guardians, staff, schools, vendors, and community partners.
  • Communicate transportation updates, delays, and service changes promptly and professionally.
  • Address concerns proactively and escalate issues when appropriate.
• Step In When Needed
  • Maintain required driving credentials and endorsements.
  • Serve as a backup driver when operational needs require additional coverage.

Requirements

• High School Diploma or equivalent required; Associate's or Bachelor's degree preferred.
• Valid driver's license with a satisfactory driving record.
• Ability to obtain and maintain Connecticut PPEC and V endorsements.
• Ability to meet all applicable Federal DOT requirements.
• Reliable personal vehicle and required insurance coverage.

Qualifications

• Previous supervisory experience preferred.
• Experience in transportation operations, dispatching, scheduling, logistics, fleet management, or a related field preferred.
• Strong leadership, communication, organization, and problem-solving skills.
• Ability to make sound decisions in a fast-moving environment while balancing multiple priorities.